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On my evening commute home from work I pass a sign for the Oregon lottery. The billboard has a large screen where the amount of the jackpot is shown in big red numbers. Not every night, but most nights the sign catches my eye and instantly carries me away to a make believe world where I have crazy amounts of money. I know what Biggie said, and yes, I heard it a thousand more times with the Puffy Daddy remixes, but I simply don’t buy that mo money equals mo problems (maybe I don’t have enough money to buy it?). In fact, I would be more than willing to be a guinea pig for any laboratory in the world that would like to give me Bill Gates-style money, and then study the affects of said money on my life.

The main problem with my little lotto dream world is that in order to win the lottery, you have to play the lottery. I suggested to a co-worker that we start throwing in a few bucks here and there to buy lotto tickets each week. He loved the idea and instantly his mind swept him away to a world where he had just won the lotto.

“Oh man, if I won like $60 million, that would be about $30 million after taxes. I would pay off my house, probably buy a better car, put some of the money away for my daughter’s college fund, I’d probably have to still work…” This is where I cut him off.

“Wait a second… In your lottery fantasy you still have a job? You need to work with your 4-year-old daughter on your imagination and make-believe skills!”

In my fantasy, my wife and I never work another day in my lives. We buy a small island and travel the entire world to go snowboarding and surfing. We have houses in Tahoe, Hawaii, Portland and all over the world. We have courtside season tickets to the Blazers, and enough money left over to save the world.

But to me, playing the lottery and expecting to win is like moving to Hollywood and expecting to become a star. It could happen, but it’s most likely just a pipe dream. But isn’t that dream worth indulging every once and awhile?

I traditionally only play the lotto when it has grown to some ridiculously large dollar amount. The type of number that even has my parents‑ who claim the lotto is a waste of money‑ asking, “Did you buy a lotto ticket.” The last time I bought a lotto ticket, I think the jackpot was over $300 million. When it gets that big, it gets everyone’s attention; which is why it is so stupid to buy a ticket then. I’d have much better odds playing the “small” jackpots. But the small jackpots don’t indulge my fantasies the way the big ones do.

Although the entire world had probably bought tickets, it didn’t stop me and my roommates from playing. I didn’t win, obviously, but the money I spent on tickets was well worth the daydreams they provided of me being filthy rich. A group of steel workers in Pittsburg won and I heard on NPR that a few of them actually showed up to work the next day. They tried to paint the winners as good guys who didn’t want their other coworkers to fall behind because they were short staffed, but I’m sure the only reason they showed up at work the next day was to constantly remind everyone, “I’m rich, BITCHES!”

The first time I played the lotto was the weekend after I graduated from college. I pulled into a gas station to buy beer and saw a sign for a $72 million jackpot. I thought it was a sign, I knew I was going to win. So I bought some tickets and spent the weekend planning my trip around the world on my new sailboat, which I was going to buy with my winnings. At the end of the weekend, it was announced that some other person won my voyage.

It is such a long shot, and the people who win usually die young and or go broke, but there’s still an allure to me. Who knows, maybe it’s the millions of dollars. But it’s not the money and the possessions that really indulge my fantasies, it’s the thought that I could make my own reality, do whatever I wanted to do for a living, not simply log hours behind a desk to pay the bills and mortgage. But my wife claims that she would still work even if we won the lotto. She said she would get bored without a job. I told her that’s fine, and I would support her decision. I also promised to call her every night, because I would rather be bored sitting on a beach in Fuji, than keeping myself busy behind a desk.